My First Anal Story

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My First Anal Story
How old you were, with who it was. How it was, did you enjoy it?
Girls, at wich age you had your first anal sex?
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Home > Sexuality > Girls, at wich age you had your first anal sex?
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25. It was my very first sexual encounter, and I was so nervous that I went numb down there. I didn't even feel anything, even though his dick was 8" with a girth that I had trouble blowing him. It was disturbing that I couldn't feel a thing. The only thing I felt was when he went limp inside me.
Maybe he did it slowly and careful, or your ass is wide. It doesn't have to hurt" I think
It should've hurt, or at least I should've felt something. Because when I finger myself or played with a dildo in my ass, it sometimes hurts. And the dildo was not as thick as him. Also, I was really numb as I could't feel anything. Not even when he was fingering my vagina. It was so bizarre
I was 20 I actually did enjoy it, we switched to anal because vaginal penetration was too painful.
18 and I didn't enjoy it because it was surprise anal
Not sure if I would say lol after that question.
20. I enjoyed it but for some reasons his penis kept slipping out from my butt.
'In' and 'Out' action is REALLY amazing!! My GF was 'teasing' me, just dipping in and out with a little ribbed toy, and she made me cum so hard I had to tell her to stop!!!
I was 18 and it was my bf, and it was different, but not uncomfortable, because I gave him cues on when to go and when to stop.
i have never had anal sex. i've heard mixed reviews about it
19, a guy I'd been sleeping with. I've done it over a dozen times with 3-4 guys and never grown to like it.
Never, and never will. If guys want to do that then go be with a another man!
22 and it did not hurt but I didn't like it either

Girls, can you describe the first time you tried anal? How did it feel what did you think?
Girls, What was the first time you tried anal like? First time a guy put a finger or tongue in there?
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Home > Sexuality > Girls, can you describe the first time you tried anal? How did it feel what did you think?
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It felt like I was taking a giant shit except it hurt really bad and I could feel him ripping me. It hurt like a bitch, and I started crying, and I couldn't move for a little bit because it hurt so bad. The next time, we did our research and used a lot of foreplay, a lot of lube, and butt plugs, but it still felt terrible. It hurt at first, but then the pain went away. Then I just felt like I was pooping the whole time and it was super gross and weird. It didn't feel good at all. I had goosebumps and I legit felt like I was coming down with the flu. I've tried and tried because my boyfriend is really into it, but even when it stops hurting and I feel fine, anal just isn't for me. I don't get any pleasure from it. It just makes me feel sick.
Well i tried it for the first time about a week ago and stupidly enough my bf just went along shoved the whole thing in there (he did have lube) and i just screamed and it took about a minute for me to not feel like i was dying of pain but i still wanted to carry on i just made him put little bits in at a time and it was fine i enjoyed it and i liked how i just surprised my bf by saying lets do anal
Well, I'm probably different from the other females. Because I love anal sex lol. The First Time I tried it I actually suggested to my ex. He was a little iffy but I got him to want To try. But I already would play with my ass when I masturbate so when we did it it wasn't that Foreign. And yeah It did hurt at first because he was pretty big but eventually once I got adjusted it felt really good. I was more enthusiac about anal sex than when I lost my virginity. So I support anal sex xD.
All I'm gonna say is it hurt like hell. Worse than when I gave my virginity up. It's not my favorite way to do things.
I've tried it a few times but will never do it again. Sexually it did nothing for me and it hurts like hell.
It was uncomfortable and made me have to take s dump afterwards. Not worth it to me.
Painful as ****. NEVER doing it again
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My mother stands ironing in the kitchen. There is barely room to squeeze between the kitchen counter and her bottom. I am about twelve; she is five foot two. It would be unnatural to turn to face the cupboards as I slip past. I am wearing loose-fitting pants. She is in a skirt. As I brushed quickly by she bends to iron and presses her bottom against me. My penis swells with joy. I will remember this for many years to come, in unexpected situations, soothing, erotic, violent, or clumsy.
It also reminded me of an earlier time, in third grade, when Tawny Collie—that was really her name—the sexiest girl at Elbow Elementary bent over to pick up a red rubber ball during recess and a couple of my friends pushed me onto her behind and she turned around and said, “Clancy, that’s not nice!” I protested, and my friends laughed. In first grade Tawny had had a crush on me and had invited me over to her house at lunch for fish sticks, which I couldn’t eat. But by third grade I was well established as one of the unpopular kids, and flying below everyone’s sexual radar. Still, or for that reason, Tawny should have known better.
The first time I successfully masturbated I was eleven and my older brother and his girlfriend were watching Woody Allen’s Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) .
Last night our little brother, as my stepsister Teryn told the story the following morning, had come downstairs while the rest of us were out and Teryn was alone watching television in the family room and asked her to “pull on my thing.” The thing was on full display, Teryn claims, out of the pajamas. “It was hard and he was rubbing it.” The little brother was age nine or ten. It is widely known or at least agreed in my family that Teryn is a liar and will lie in particular about this little brother, because she was the baby until we arrived, and then he became the baby, and my mother has never liked Teryn, and often accused her of sexual deviance and promiscuity from a surprisingly young age. So there’s no guessing whether or not the story Teryn tells me is true, though later in life my mother will similarly tell me that she saw the same little brother (now age sixteen) out mowing the lawn with his shirt off in the low, modest Calgary summer sun and pronounced fiery claw marks down his back. Why my mother told me this story also remains mysterious to me, though she once told me that “he got the looks, he could have been a model,” and another time she told me how much he resembled my father, who had no appeal for my mother other than as a sex object. He was a terrible husband, my dad. But the old man had gigantic sexual charisma. I’d seen him, in years past and in many different cities, pick up waitresses right there in the restaurant, before we’d even paid the check.
The first time I successfully masturbated I was eleven and my older brother and his girlfriend were watching Woody Allen’s Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) . The process was slow and often seemed hopeless: I think it took an hour or more. I could still hear the movie in the background. I imagined my penis as a straw and a girl from school sucking on the straw. When I orgasmed it was qualitatively different than any orgasm I have had since. They say that, the first time you smoke heroin, it is called “riding the dragon,” and after that you are always only approximating that birth into a new world of pleasure and disappointment.
You can French kiss yourself. Take your tongue, fold it back upon itself, and now roll the tip of your tongue back and forth across the middle of the muscle. I learned this after French kissing Denise at the seventh grade dance. We had those at Rideau Junior High: every five or six dances the teachers would play a slow song, turn the lights down low, and we would have a kiss dance, during which, with luck, you would French kiss the entire time. I passed Denise’s house wearing my canvas bag of rolled and rubber-banded Calgary Heralds and tossed one on her porch, while French kissing myself. It is mildly titillating, but seems filthier, somehow, than masturbation.
In graduate school I decided to become gay. Many of my heroes were gay: I had thought Franz Kafka was gay, for example, though it turns out he probably was not.
Age five and I am inspecting statues of nudes in a large museum book my parents keep in my stepfather’s study. The book is fascinating and I take it back to my bedroom and climb on the top bunk—my bunk—to look at the pictures more closely. The fact that the most interesting statues—the ones with breasts—have no penises puzzles me. In the bathroom I stand naked on the toilet so that I can see myself in the mirror and tuck my penis and balls between my legs and press my legs tightly together to achieve the desired effect. Ah yes, that must be what is happening in those pictures, I conclude. Then my mother enters the bathroom—there are two doors into it, one from the hallway and the other from my parent’s bedroom, and I’ve forgotten to lock their door—and begins to shriek. “Never do that again! That’s very bad!” Etc. To be fair to my mother, she has always been hysterical and repressed on the subject of sex (I don’t particularly like the topic either), and my father claimed that this was a main cause of their divorce. It’s true that she avoided physical contact with us for years. She had been abused as a child, though I don’t know in what fashion. On her wedding night there were some problems in bed with my father, and he left their hotel room, returned a few hours later, and threw a pair of woman’s panties at her.
After my mother married my stepfather there are some sexual experiences between age five and age fifteen that I do not recall well and may be inventing that took place between myself and one or more of my angry older stepbrothers behind the furnace in our basement. I was terrified of that small black hot space.
In graduate school I decided to become gay. Many of my heroes were gay: I had thought Franz Kafka was gay, for example, though it turns out he probably was not; Kierkegaard might have been gay; it is possible that Friedrich Nietzsche’s first sexual experience was with a man, a kind of wandering prophet, a forester who walked with a stick and professed to be a wise man, and preyed on school boys; Oscar Wilde was gay; Marcel Proust was gay (I’m told that stuff about the rats and the hookers is invented); Jean Genet was gay; Burroughs was gay (William—Augusten is too, but, capable writer though he is, he’s not a hero of mine, and anyway hadn’t made the scene yet when I was in graduate school, or who knows, perhaps he might have been, I was in the hero-forming business in those days); was Levinas gay?; Plato was gay. My best friend at the time, Robert Ramirez, was gay, and wanted me to be gay too. (Now he is dead.) We danced at a gay bar and while I was dancing with a girlfriend of his, a hanger-on, he came to us on the dance floor under the many-colored lights, the celestial immodesty and grandeur of the sweaty, loud gay bar, and the three of us danced with the girl in the middle, and Robert and I kissed. Nothing. All my modest attempts were useless. Later that night the girl and I had sex—she was a virgin—and Robert’s feelings were hurt that we didn’t ask him to join us. First he passed out and then he stormed out. I never spoke with the girl again. I abandoned the idea of being gay. William Butler Yeats was not gay.
SD and I were in the basement in her bedroom. She was encouraging me to rub my erect penis on the crotch of her black panty hose. She was a natural redhead. When she took off her clothes her slightly fat body shone with the strength of a flashbulb in my eyes. She rolled on her belly, moaned, and lifted her ass in the air. “In my ass,” she said. I had anal sex before I ever had vaginal sex: that was how I lost my virginity, that winter afternoon in SD’s ass.
Clancy Martin ’s writing has appeared in Harper’s , NOON , McSweeney’s , The London Review of Books , the New York Times , and other places. Author of the novel How to Sell (FSG), he teaches philosophy at the University of Missouri in Kansas City.


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Losing your virginity is a big deal. I remember my first time like it was yesterday. Not only was it painful the first time, but it hurt like hell a few times after that. I soon realized that it was not at all like how the movies portrayed it to be.
No matter how old you are when you decide to pop your cherry, it’s a very intense moment. Things can get interesting and your very first time is one you’ll never forget. A relationship writer spoke with a few adults about their first time. From being scared as sh*t, to just wanting to get it over with, women and men talk about the first time they had sex.
I was a junior in high school and had been with my on-and-off again high school sweetheart. He was extremely respectful of me and my body. I always felt safe and protected with him. We had a couple close encounters before – making out then eventually into oral sex – but I told him I refused to lose my virginity in the back of a car so it was what it was. The week of Valentine’s Day, it was clear from our body chemistry that we weren’t going to be able to put it off much longer so that weekend, we went shopping and eventually went over to one of his really good friend’s house for a couple’s movie night. His friend’s family had a theater in the basement with an attached guest bedroom so that was the scene of the magic. When we finally went in the room, I wasn’t nervous but I was afraid from our most recent attempt that my first time might hurt. I took control, got on top, and eased my way down. He was very gentle with me, making sure I was okay, until I no longer wanted him to be gentle.
The soundtrack was whatever movie was playing. But in my mind, the song that I knew I would lose my virginity to was “Take It Off (Dim the Lights)” by Pharrell, an album that I was absolutely obsessed with at the time, so that’s what I fantasized about while we were doing it. When it was over, I was expecting the world and the universe to shift, but I pretty much felt the same as I had always felt, just normal. I was excited to share with my friends that I had finally been initiated as a woman but even then, I don’t think I said anything until weeks later. I felt just as close to my boyfriend then as I had always been, and although I knew that he wouldn’t be my husband or anything, I was and am still, very happy to have given my virginity to him.
Credit: wavebreakmedia/Shutterstock
My earliest sexual memory was when I was 8, I was young (laughs). I think my classmate wanted me to touch his penis in exchange for some candy. I was like, I wanted some candy, he has some candy, so I’ll touch his penis. Even when I was young, I remember dry humping with people. I can’t remember my first taste of sex, but I remember I was really young. I lost my virginity when I was 19. I don’t know how to word this, but this person was the first man I ever felt comfortable with outside of the males in my family. At this point we weren’t even quote unquote together, we were just friends. I developed really strong feelings for him and vice versa. I was really comfortable with him, he was just different. He didn’t make me feel like I had to be guarded, or scared, or nervous. I was just really comfortable which is probably why that came about. Because of previous trauma, I had a detachment to sex. I felt like sex made girls damaged. I had a misogynist view of a woman being touched sexually and that making her “destroyed”.
I thought sex was taboo and a thing people did to be nasty. That was all prior to him though. I wasn’t afraid to lose my virginity. I was ready. I hadn’t heard a lot of horror stories. The people I had known who had lost it had really exciting, thrilling stories about it. I would always hear, “You know when you’re ready”. I remember it hurting. I remember overthinking it, like what if he doesn’t like me after this? What if it’s not good? Physically, it hurt at first, but it was like a welcoming pain, like (sighs), I can deal with this pain
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